1-carboxycyclohexylphenylmethanone | 855428-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-carboxycyclohexylphenylmethanone
• 英文别名: 1-Benzoylcyclohexane-1-carboxylic acid
• CAS: 855428-40-9
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: HXPVTDPSOSOYCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-carboxycyclohexylphenylmethanone 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  The introduction of P4 substituted 1-methylcyclohexyl groups into Boceprevir®: A change in direction in the search for a second generation HCV NS3 protease inhibitor

  摘要：

  In the search for a second generation HCV protease inhibitor, molecular modeling studies of the X-ray crystal structure of Boceprevir (R) 1 bound to the NS3 protein suggest that expansion into the S4 pocket could provide additional hydrophobic Van der Waals interactions. Effective replacement of the P4 tertbutyl with a cyclohexylmethyl ligand led to inhibitor 2 with improved enzyme and replicon activities. Subsequent modeling and SAR studies led to the pyridine 38 and sulfone analogues 52 and 53 with vastly improved PK parameters in monkeys, forming a new foundation for further exploration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.063
• 作为产物：
  描述：

  methyl 1-benzoylcyclohexanecarboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-carboxycyclohexylphenylmethanone
  参考文献：
  名称：

  The introduction of P4 substituted 1-methylcyclohexyl groups into Boceprevir®: A change in direction in the search for a second generation HCV NS3 protease inhibitor

  摘要：

  In the search for a second generation HCV protease inhibitor, molecular modeling studies of the X-ray crystal structure of Boceprevir (R) 1 bound to the NS3 protein suggest that expansion into the S4 pocket could provide additional hydrophobic Van der Waals interactions. Effective replacement of the P4 tertbutyl with a cyclohexylmethyl ligand led to inhibitor 2 with improved enzyme and replicon activities. Subsequent modeling and SAR studies led to the pyridine 38 and sulfone analogues 52 and 53 with vastly improved PK parameters in monkeys, forming a new foundation for further exploration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.063

文献信息

• [EN] PIPERIDINE-PYRIDAZONES AND PHTHALAZONES AS PDE4 INHIBITORS<br/>[FR] PIPERIDINE-PYRIDAZONES ET PHTHALAZONES EN TANT QU'INHIBITEURS DE PDE4
  申请人：ALTANA PHARMA AG

  公开号：WO2004017974A1

  公开（公告）日：2004-03-04

  The compounds of a certain formula 1, in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  某种化学式为1的化合物，其中给定的取代基具有描述中所示的含义，是新颖有效的PDE4抑制剂。
• [EN] PIPERIDINE-N-OXIDE-DERIVATIVES<br/>[FR] DERIVES DE N-OXYDE DE PIPERIDINE
  申请人：ALTANA PHARMA AG

  公开号：WO2004018450A1

  公开（公告）日：2004-03-04

  The compounds of a certain formula (1), in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  具有特定化学式（1）的化合物，其中给定的取代基具有描述中指示的含义，是新颖有效的PDE4抑制剂。
• Piperidine-pyridazones and phthalazones as pde4 inhibitors
  申请人：Sterk Geert Jan

  公开号：US20060094710A1

  公开（公告）日：2006-05-04

  The compounds of a certain formula 1, in which the given substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  某种化学式为1的化合物，其中给定的取代基具有描述中指定的含义，是新颖有效的PDE4抑制剂。
• Pyrrolidinedione substituted piperidine-phtalazones as pde4 inhibitors
  申请人：Sterk Geert Jan

  公开号：US20060160813A1

  公开（公告）日：2006-07-20

  The compounds of formula I in which the substituents have the meanings as indicated in the description, are novel effective PDE4 inhibitors.

  具有描述中所指示的含义的取代基的I式化合物是新颖有效的PDE4抑制剂。
• Piperidine-n-oxide-derivatives
  申请人：Sterk Jan Geert

  公开号：US20060166995A1

  公开（公告）日：2006-07-27

  The compounds of a certain formula (1), in which the given substituents have the meanings as given in the description, are novel effective PDE4 inhibitors.

  某一公式（1）的化合物，其中给定的取代基具有描述中所给的含义，是新颖有效的PDE4抑制剂。